HCID 90928462, compound → HCID 69054321, compound

HRID 2100632Notes

Reaction equation

HRID 2100632 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][C@@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@H:7]3[C:6]=2[CH:5]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.[CH:31]([Zn]C(C)C)([CH3:33])[CH3:32]>C1(C)C=CC=CC=1.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[CH:31]([C:4]1[CH:3]=[C:2]([CH3:1])[C:11]2[C:10](=[O:12])[NH:9][C@@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@H:7]3[C:6]=2[CH:5]=1)([CH3:33])[CH3:32]

Participants

6

Reactant 2

HCID 90928462HCID 90928462, compoundHCID 178461828HCID 178461828, compound

Product 1

HCID 69054321HCID 69054321, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (±)-trans tert-butyl 6-methyl-5-oxo-8-(trifluoromethylsulfonyloxy)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 91, Part A (265 mg, 0.59 mmol) was added diisopropylzinc (1.76 mL of a 1.0 M solution in toluene, 1.76 mmol). The reaction mixture was degassed with a stream of argon and then there was added bis(diphenylphosphino)ferrocene]-dichloropalladium (II) (22 mg, 0.029 mmol). The reaction mixture was allowed to stir at 65° C. for 18 h. The reaction was allowed to cool to ambient temperature and was quenched with 1N HCl. The mixture was diluted with ethyl acetate and the organics were washed with brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.22 g of the title compound as an off-white solid, which was sufficiently pure to be employed directly in Part B. LRMS (ESI): 345.2 (M+H)+.

Workup

  1. customThe reaction mixture was degassed with a stream of argon
  2. temperatureto cool to ambient temperature
  3. customwas quenched with 1N HCl
  4. additionThe mixture was diluted with ethyl acetate
  5. washthe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c6649a4fe1e4a268479bfc75b3b3083
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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